Lesli's Story - Part 1
I've never been comfortable with the "gay" label, even though I had my first sexual encounter with another boy at the tender age of 17. And it's not because I don't like labels, I have nothing against them, I think they play an important part of how we describe ourselves. To be truthful, I've never really been comfortable with "gay" sex, or at least with what I considered to be "gay" in the normal definition.
And that's what this story is all about.
I was a "normal" child by all accounts, no overbearing mother, not abandoned by my father. Just normal.
The desire to dress began with the approach of puberty. It started, innocently enough, with a facination with my older sister's wardrobe. I had seen her in underwear many times over the years, but as I grew older, I started to envy her and wish I could dress as she did. It started with the fantasy of imagining myself in panties, bra, and a dress and quickly progressed to the point where I actually stole a pair of her panties from the laundry basket one Saturday. It was all so easy, she had some many clothes she surely wouldn't miss one pair of panties.
They were white, silk, high cut bikini panties, and the feeling as I pulled them over my naked legs was electric. I almost climaxed with excitement as I pulled them snug against my bottom, my penis and testicles fitting tightly in the confined space meant for a girl. In all the years since, I have never felt such a change take place as I did that Saturday. I recognized this later as the beginning of a long journey from a confused boy to the wonderful world of transvestism and, later, the realization of my transexual self.
Of course I couldn't stop there, and over the course of the next few weeks, I managed to steal and stash away other things - first a bra, white to match the panties, and then a skirt and blouse. I dressed late at night, after everyone was asleep, and paraded around my room modeling each new acquisition. I didn't have the slightest idea why I felt as I did, why I was motivated to do these things. But I didn't care, I was so excited by the dressing that I didn't think of anything else, waiting impatiently for my family to go to sleep so I could slip into my world of girls clothes.
My sexual feelings developed with my dressing, and I found myself fantasizing all sorts of encounters with boys and men with me as a girl. In my fantasies I was beautiful, like Charlie's Angels, and completely dominated by the men in my life. Since I never had a sexual experience with a girl, I could only imagine what boys would do to me, what I would do for them. With no exposure to pornography, this was pretty mild and consisted mostly of fantasies of being kidnapped, tied up, the usual soft kind of stuff.
This innocent dressing and fantasizing went on for the next few years and I enjoyed it more and more, eventually fantasizing to orgasm, dressed.
Of course, life doesn't revolve around fantasies, and the reality of it bore down on me til I realized that the dressing was a small part of it, albeit important. High school takes it's toll on us all, the sexually confused more than others, and although I didn't consider myself suffering, my sexual identity did have its ups and downs. Confused is a better description, I suppose, but I did manage a rather "normal" teenagehood.
I can't complain.
Male to male sex was something that had never appealed to me, but as I grew older I began to fantasize about it as well, and by my senior year in high school I was open to the possibilities. There was but one "outed" queer in my school, and I fantasized about making out with him. I was confused by the fantasies, yet excited about what I felt. I didn't have the nerve to approach him, the realization that associating with him would brand me as well. No, I secretly lusted but never outwardly approached him.
Keep in mind that I wasn't a football player, a track star, or a macho type guy. I was an average sized person void of the usual body hair, not effiminate but not athletic. In short, average. At least to me.
I don't know how people gauge other people in things like this. I understand, at least now, body language, imperceptible sexual signs, subliminal communication. How Kenneth saw through me though I have no clue.
But he did.
We were friends, good friends who shared the usual experiences of high school. Girls, camping out, sleeping over. Nothing but the normal. It went past that one Saturday night just past my 17th birthday.
Kenneth and I had double dated that night. A night with two girls at the drive in and then a sleep over at my house. We had scored the usual six pack and bottle, even though we were underage. The girls didn't drink much, so we had done the honors. By the time we fell into bed we were both drunk. And since neither of us had scored, we were hot.
I would come to realize later just how hot we were.
We engaged in the usual small talk before going to sleep, but as it revolved around girls, sex, and rock and roll, the tone increasingly turned to sex, with Kenneth complaining that he had tried and tried, unsuccessfully, to get his date to either jerk him off or go down on him. I lied that I had done the same. Truth be told, I hadn't done anything other than kiss her.
"I sure need a girl" Kenneth sighed as he laid on his back next to me "do you know where I can get one?"
"What would you do?" I asked, about to pass out.
"I want a girl to suck my dick" he replied "to take it in the mouth".
"And what would you do for her ?" I toyed, my alcohol fogged emotions starting to work out alternatives.
"Are you offering me something?" he countered, brushing my thigh with his hand, which lit my fire.
"Ummh...don't know" I managed, not sure of what I was, indeed, offering.
"God, I need to get off" he went on, "will you get me off?"
The offer, the request - and I've learned to accept them now with a certain degree of diplomacy - was out of the blue. I didn't have the first clue.
"How?" I asked, genuently puzzled-but somewhat excited-at the possibility.
Give me a break here, I had fantasized during my dressing - I had imagined myself as a girl, a sexy wanted, beautiful girl. What was I supposed to do when a boy asked me to be what I had fantasized about being? Was I supposed to revert to a macho, hetro role? Or was I supposed to react in the manner I had been fantasizing about for the past 3 years?
Duhhhhh?
Kenneth pressed my head down to his crotch and my lips parted to accept the head of his swollen cock. Within a heartbeat my lips had opened to accept the head into my mouth, and before I could begin to enjoy my first blowjob, he erupted into me. His first spurts filled my mouth to the limits with the sweet, thick cum that I would come to expect as the reward for a job well done. As inexperienced as I was I still managed to swallow his entire load.
I must admit that this first experience was over before I had a chance to savor the reality of it, and I was honestly left with a feeling of denial. That would not last long.
I would soon come to realize that I had wanted it as much as he did. But now, the act over, the taste of cum still strong in my mouth, he rolled over and was soon fast asleep. Not me. My emotions were still running high, my alcohol fogged mind still working to process what had happened...my God, I had sucked his dick...I replayed it over and over before finally drifting off.
It was as if it had never happened the next morning. Slightly embarrassed, we both made small talk before parting. But it was still vivid in my mind.
It had seemed so natural at the time, I mean it seemed like what I should do. And it seemed beautiful that I had done it for him, relieved him like I did. I know it had made him feel good, and that made me feel good. Later in life I would come to the realization that giving pleasure to men gave me an intense sexual power trip. But, I couldn't say that I was wild about the act. At least not at first. But again, I had done for Kenneth what girls do, and it made me feel more feminine having done it. And the illusion that by doing girl things I would become more like a girl was the thing that kept me going until before I knew it I was enjoying the act.
The next few days were awkward for both of us. At school we hardly spoke, and never about what we had done....or more precisely what I had done. I was in a state of denial. Not comfortable with it, not trying to convince myself it was right or wrong, but Kenneth seemed to come round to it before I did and coaxed me to ride home with him after school on Wednesday.
"I, uh, well, I, uh, uh, sort of enjoyed that...you know, what you did" he began.
"You mean what we did?" I interjected, not wanting to make it seem as if I had been the aggressor.
"Yeah, uh, I mean what we did" he admitted. "Would you do it for me again?" he asked, obviously wanting it.
"I guess so" I said softly "but nobody can know. Promise?"
"Of course" he replied "no one will ever know. It'll be our secret. I have to go to work now, but I'll be off at 7. Let's go for a ride."
"OK, I'll be ready."
I went straight to my room, locked the door, and dug through the closet for my panties and bra which I kept hidden in my gym bag. Within minutes I was admiring the clean cut of the bikini panties as they hugged my hips and bottom. My ass really looked like a girls, rounded in just the right places. I tucked my penis and balls between my legs, nothing showing to disturb the illusion of a girls organ down there. I pulled the bra tight, creating the slightest bit of cleavage in front. As I examined my form in the mirror, I was struck by the fact that I did look like a girl! My body was small enough, and I had curves in enough of the right places to actually pass for a girl. My hair was shoulder length, in the style of the day, definately a unisex look. But with the right clothes everything fell into place. Stepping into the short skirt and pulling on the white silk blouse completed the transformation. I had to admit it, I was a good looking girl!
Passable or not, I wasn't ready to go out in public like this. I needed more practice, and much much more confidence before I tried that. And besides, I wasn't at all sure how Kenneth would take all this. So reluctantly I took off the skirt and blouse and put them back into hiding.
Neither my parents, nor my sister were at home yet.
Still feeling girly, I drew a bath in my sister's tub and soaked for a few minutes before taking her razor to my legs. Not that I needed it, my legs and arms were as smooth after the shave as before, but the feeling was positively feminine. The combination of the warm bath and freshly shaven legs had me sexually aroused and looking forward to my "date" with Kenneth. For good measure I shaved my pubic hair into a small vee just above the base of my penis, and carefully removed the light fuzz from my ball sack.
I redressed, panties, bra, jeans, and a loose fitting T shirt, no socks, and a pair of thong sandals. Using my sisters hair brush, I brushed until my hair was straight, then pulled it back into a pony tail, securing it with a rubber band. Checking myself in the mirror, I was surprised at the look. Unisex, but slightly on the feminine side. first. I definately didn't want to face my parents looking like this, so I decided to hide in my room til just before 7 and slip out the window to meet Kenneth.
"Uh....wow....you look like a...a...well, you look sorta like a girl...only a lot like a girl" Kenneth stammered as greated him at the corner near my house. I slipped into the passenger seat as he drove off.
"Thank you" I replied "I sort of feel like that too". It was true. While I had enjoyed what we had done before, I really looked forward to doing it dressed like this.
There were plenty of makeout spots around town, but not wanting to take a chance, Kenneth drove out of town and into the country. We took a turn onto a small country road, then on for a few miles until the road turned up into the woods. Within a mile, we took a turn off the main road onto a dead ended logging road. Kenneth cut the lights and turned off the ignition.
Blackness engulfed us like a dark mine shaft. As we sat there in the darkness, the only sounds were those of the crickets. We both sat silent, as if we were trying to work up the courage to do whatever it was we knew we were going to do.
Finally, Kenneth spoke, his voice coming from the darkness to my left. "Let's get undressed and get in the back seat where there's more room." He sat on the seat, his legs out the opened driver's side door as he stripped off his jeans, socks, shirt and underwear.
I stepped out my side and pulled my tee shirt over my head, unbuttoned and removed my jeans, leaving me in just my panties and bra.
"Wow" I heard him exclaim as I slipped into the backseat beside him "you look just like a girl". Those were the sweetest words I had heard in my life! Taking my hand in his, he pulled it down to his crotch, and I was surprised to find his penis erect. Encircling it with my fingers, I pulled gently back and forth, from the base to the head. I had never really examined another boy's penis before, so I took the time to fondle and explore his manhood as I slowly jacked him. It felt good, and I found myself getting really, really turned on. He was too, I could tell from his breathing.
And he was ready. Putting his hands on my shoulders, he pulled my head down until my face was at his dick. Of course I knew what he wanted, and I decided I wanted it too, so I opened my mouth and took the head in. It tasted slightly salty to my tongue, and I opened wider to get more of him inside. Remembering our encounter of a few nights ago, I forced him inside, thinking all the time that he would shoot quickly and I wanted him completely inside me. But he surprised me by pulling my mouth off his dick and getting out of the car.
"Don't want to make a mess in Dad's car" was his explanation as he turned to lean against the driver's door. Taking my cue, I got out of the car and knelt in front of him, the leaves cool on my bare knees. I barely had my mouth open when he shoved his dick in it, gagging me. I jerked my head back, pulling it out til it was half inside my mouth and half outside, reaching up with my hand to grasp the shaft. This was more comfortable as I could regulate how much went inside.
That was a defining moment for me, on my knees, with a cock in my mouth. I would come to this situation many times in my life, but this was the first, and it occurred to me that my real life had just begun. Gone was the uneasiness with male to male sex. This was male to female sex, I was the female. And I would give the maximum pleasure to my male lover.
For the first time in my life I felt like I belonged here, felt really, really wanted, enjoying what I was doing. In short, I felt as if I had discovered myself, my role in life.
And for the first time in my life, I was aware of the manhood I would come to worship. The taste, the feel, the pleasure that a man's penis could be to me. My tongue explored every vein, the head, the soft sensitive underside, and the long, beautiful shaft that slipped everso deep into my mouth until it was finally pressing against the back of my mouth and then, magically, sliding into my stretched throat.
I was, in essence, in heaven, and on auto pilot as Kenneth thrust - and I pulled - his cock in me. Moistened with my saliva, his manhood slid easily in and out of my hot, willing, accomodating mouth as my fingers gripped the shaft and added just the right amount of friction to keep him rock hard.
But Kenneth was not an experienced lover - at this point - and soon, too soon, I felt the first warm spurts as he ejaculated in my mouth. I kept up the tempo of the blow job, pausing occassionaly to swallow his sweet, sticky load. The taste was salty but not at all unpleasant and I was surprised that I did not gag.
I sucked and ate all of his jism, not wanting to waste a drop. I was again surprised at how easily I did it.
In no time he was soft, pulling his limp dick from my mouth as I struggled to keep it there. Exhausted, he pulled his pants back on and I did the same.
"That was great" he offered as we drove back to my house "you really know what you're doing. You suck....and look like a real girl."
"It was only the second time we've done it" I replied.
"Well, it sure as hell won't be the last. I mean...if it's ok with you".
"But no one can find out, ok?"
"Sure" he reassured me. "No one will suspect you're not a girl if you dress like that."
"Oh, I can look even better" I offered, remembering how I looked earlier tonight in a skirt and blouse.
To be continued.........